Pineapple Upside Down Cupcakes

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Cupcakes are all the rage!  These baby cakes are being served everywhere. You can find them on the dessert table at family meals or even at weddings. It doesn’t surprise me that people love cupcakes. When you can pick up a sweet treat and eat it with your hands you have found the pot of gold.  And these pineapple upside down cupcakes are delicious. This post may contain affiliate links.  Pineapple Upside Down Cupcakes are all the rage! These baby cakes are being served everywhere.   Pineapple Upside Down Cupcakes have become my husband’s new favorite dessert. I’m a chocolate loving kind of girl, but can definitely eat my way through a few Pineapple Upside Down Cupcakes when the opportunity presents itself.

You will need a few simple ingredients to get you started. 

Yellow Cake Mix (eggs, oil, water) Whatever your particular mix calls for


Brown Sugar

Crushed Pineapple

Maraschino Cherries 

Something to grease your cupcake tins with. (I use Crisco, but a good non-stick spray should work, too)

You will need to have some wax paper on hand so you can invert the cupcakes onto the wax paper when releasing them. 

Pineapple Upside Down Cupcakes

Here are a few tips to make this recipe work better.

When mixing these cupcakes if your cake mix calls for the water you will be replacing it with the pineapple juice you drained from the can. If you don’t have enough juice just add water until you get to the right measurements.

Be sure your cupcake tins are well greased. This will prevent sticking. 

When you add the butter, brown sugar pineapple and cherry push it down with the back of a spoon so it’s an even layer. 

Put these on the middle oven rack. 

If you are using a dark pan reduce your cooking temperature by 25 degrees. 

Let the cupcakes cool for 5 mins before inverting them. 

Following those few tips will ensure that these cupcakes will be a new family favorite if you can keep them around long enough for everyone to try! 

Curious minds want to know, Do you eat the cherry on top of your pineapple upside down cake?

I do not! If it was a chocolate covered cherry I’d probably eat it. But it’s a big no on maraschino cherries for me!

Yield: 24

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes


  • 1/2 cup butter, melted
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 20 ounce can crushed pineapple drained
  • 1 box of your favorite yellow cake mix
  • 3 eggs
  • 1/3 cup oil
  • 1 1/3 cup pineapple juice


  1. Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F.
  2. Grease 24 muffin cups. (Try using shortening or a good non-stick spray)
  3. Line a work surface with waxed paper
  4. Spoon 1 teaspoon melted butter into the bottom of each muffin cup.
  5. Spoon 1 tablespoon brown sugar in each muffin cup.
  6. Press a maraschino cherry into the center of the brown sugar in each muffin cup.
  7. Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.
  8. Mix yellow cake mix as directed adding in your oil, eggs, etc.. replacing the water with pineapple juice until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
  9. Pour cake batter into the muffin cup, filling them almost to the top; do not overfill.
  10. Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
  11. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the wax paper to release. Serve with pineapple and cherry sides up.


The oil and eggs are listed in the ingredients because every yellow cake mix I have ever used calls for those ingredients in those measurements. You may have to adjsut the ingredients accordingly depending on the cake mix you use.

Crushed pineapple works best.

Nutrition Information



Serving Size


Amount Per Serving Calories 225 Total Fat 8g Saturated Fat 3g Trans Fat 0g Unsaturated Fat 4g Cholesterol 33mg Sodium 202mg Carbohydrates 37g Fiber 1g Sugar 27g Protein 2g
As with any of our recipes, carb counts, calorie counts, WW points and nutritional information varies greatly. As a result, your nutritional content depends on which products you choose to use when cooking this dish. The auto-calculation is just an automated estimate and should NOT be used for specific dietary needs.


Michele is a married mom of 3 adult children. She is currently enjoying spending time with her husband in the empty nest. Michele can be found working on a healthy lifestyle, camping or having some frugal fun. Not necessarily in that order!

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  • Reply
    March 8, 2015 at 3:24 pm

    first class recipe

  • Reply
    May 31, 2015 at 9:40 pm

    Mmmm, these look amazing. I’ve been toying with my mind about making pineapple upside down cake and I think these were the deciding factor. YUM!

  • Reply
    June 1, 2015 at 10:16 am

    I love pineapple upside down cake – these cupcakes are a great idea!

  • Reply
    June 4, 2015 at 11:28 am

    This recipe sounds great. I am going to get the ingredients today and make them for dinner. Thanks for sharing.

  • Reply
    Brandi Clevinger
    June 5, 2015 at 9:05 pm

    Oh yummy! I’m going to have to make these this weekend. I have all the ingredients except the cherries. My kids are going to love these! Especially when I flip it over and there’s a cherry on the bottom!

    Thanks for sharing!

  • Reply
    June 5, 2015 at 9:41 pm

    Now that is a cupcake I could enjoy. It looks nice and moist and tasty and no need for frosting. What a great idea they are. Thanks for bringing them to #HomeMattersParty I am going to pin them to remind me how to make them.

  • Reply
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  • Reply
    Bridget - The Recipe Wench
    June 8, 2015 at 12:03 am

    Wow! I had to pin these — they look amazingly delicious. Thanks for sharing at the Inspire Me Mondays Link-up!

  • Reply
    Crystal @
    June 8, 2015 at 3:51 pm

    We recently made a Pineapple Upside Down Cake for Memorial Day and it was awesome. How much cooler would it be to have in individual servings? Yummy!

  • Reply
    sharon shafran
    June 18, 2015 at 12:47 am

    makes my mouth water just looking at this recipe

  • Reply
    September 3, 2015 at 7:53 am

    When you say ‘muffin cups’ do you you mean a muffin pan or individual muffin cups without the pan? I know this is a silly question ?

    • Reply
      Michele Brosius
      September 6, 2015 at 7:20 pm

      We used a muffin pan, but have actually had much better luck making them in a silicone muffin cup. Either works! Thanks for stopping by.

  • Reply
    December 21, 2015 at 7:18 pm

    How far in advance can you make these? Is there enough juice from the crushed pineapple?

    • Reply
      Michele Brosius
      December 24, 2015 at 7:38 pm

      Yes there is plenty of juice. I have only ever made them in the AM and served them in the PM. Thanks!

  • Reply
    April 6, 2016 at 1:35 pm

    Pinned this one – my husband’s favorite dessert!

  • Reply
    April 8, 2016 at 11:00 pm

    These look delicious.

  • Reply
    April 9, 2016 at 11:48 am

    Individual servings are the BEST! These look delicious. Thanks for sharing at FTAF

  • Reply
    Jen @ upcyclednest
    April 10, 2016 at 9:42 am

    Wow, those look delicious! I’ll pin it to try later!

  • Reply
    Pamela Shank
    April 10, 2016 at 12:21 pm

    Your cupcakes look awesome. I have made these before and really like how they turn out. I think they are classy to take to a function (or just eat) and I prefer the baby cake thing anyway. Great job

  • Reply
    Helen Fern
    April 10, 2016 at 12:57 pm

    These look really delightful!! Would love to have you share it at the “What’s for Dinner” blog hop!

  • Reply
    April 11, 2016 at 4:46 pm

    Delicious looking cakes – thank you for sharing with Pin Worthy Wednesday

  • Reply
    April 11, 2016 at 10:40 pm

    These are so cute! I love anything in mini form! Thanks for sharing! #homeMattersParty

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  • Reply
    Stephanie Lett
    November 23, 2016 at 8:04 pm

    I just made these mini upside down pineapple cakes, if you could smell my house as they were baking !!!! So easy to make and quick . I am adding these tomorrow to my Thanksgiving desert table.

  • Reply
    March 13, 2017 at 11:40 am

    These are so much fun! The perfect Easter dessert to bring to the big family dinner. Thanks for sharing your recipe with us at Merry Monday this week!

  • Reply
    Pauline Molinari
    March 14, 2017 at 10:43 pm

    These cupcakes look so yummy! Thanks for sharing your tasty recipe with us this week on the Monday Funday Party!

  • Reply
    Leah Ashley
    March 15, 2017 at 3:03 pm

    These look absolutely delicious!!! A mini version on my favorite cake!! Thanks for sharing can’t wait to try!!

  • Reply
    Roseann Hampton
    March 15, 2017 at 8:12 pm

    I never thought about doing pineapple upside down as a cupcake! Thanks for sharing!

  • Reply
    Leslie Soto
    March 16, 2017 at 1:00 pm

    Hi! I’m one of the co-hosts from the Welcome Home Wednesdays Link Up. These cupcakes sound delicious! I am a huge fan of pineapple upside down cake but never thought of putting them in a cupcake. These are perfect for a summer cookout. Thank you for sharing.

  • Reply
    susan s
    May 2, 2017 at 7:18 pm

    When it says muffin cups , does that mean straight into the pan or into muffin papers?

    • Reply
      Michele Brosius
      May 2, 2017 at 11:15 pm

      Thanks for asking. I do not use papers for this recipe.

  • Reply
    Jim Trogdon
    June 22, 2017 at 6:33 pm

    Great tasting treat. I did notice though that the printable recipe does not say to drain the crushed pineapple. Glad I double checked.
    Keep up the great work.

  • Reply
    September 20, 2018 at 7:12 pm

    I can’t eat butter or margarine. Is there some other type of oil that would work?

    • Reply
      Michele Brosius
      September 22, 2018 at 3:57 pm

      Sorry I haven’t tried this recipe in any alternate forms. Let me know if you have any ideas. Thanks!

    • Reply
      Michele Brosius
      May 5, 2019 at 4:08 pm

      I don’t think so. thanks

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  • Reply
    April 8, 2019 at 1:56 pm

    Can they be made ahead of time and eaten the next day or should they be eaten fresh out of the oven and warm?

    • Reply
      Michele Brosius
      April 8, 2019 at 3:55 pm

      We always make them ahead of time. I’ve never tried them warm, but we just may have too. Thanks!

  • Reply
    April 13, 2019 at 10:43 pm

    I have been making Pineapple UpSide Down Cupcakes for several years. I always use a Pineapple Supreme Cake Mix I drain my can of pineapple and use that juice for the liquid requested to make the cake mix. Most always have enough juice but if not I just add water to the juice. Big hit when I take them to a function.

  • Reply
    May 1, 2019 at 7:29 pm

    Just made them, have a problem with them sticking to the wax paper (I used parchment paper thinking it won’t stick) but it did stick. Did I take them out of the muffin tin too soon. They look delicious and hubby said they taste delicious. So that’s good. Left them in muffin tin little over 5 min about 6 or so. Lots of the brown sugar & pineapple stuck in tin also, used butter knife to spread on cupcakes. I did get 24 cupcakes so that’s really good. Just want to know about the sticking to the paper issues. Thanks

    • Reply
      Michele Brosius
      May 5, 2019 at 4:08 pm

      I normally use the non-stick or silicone muffin pans and grease them with non-stick spray so I don’t see much sticking in the pan. (Maybe lower your oven temp 25 degrees) I’ve also never had them stick to the wax paper. Maybe non-stick spray on your parchment may help. Thanks

  • Reply
    Cathy G
    May 7, 2019 at 5:46 pm

    Mine stuck also. Used non stick pan and spray but they stuck pretty bad. They are not pretty like yours but taste great! I will lower my oven temp next time to see if that helps.

  • Reply
    Ursa ~
    September 15, 2019 at 5:01 pm

    I’ve been making them for years ~ My fiancé’ calls them PUDcakes. I usually dice up the cherries so that you get a small bit of it in each bite.

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